Uncommitted: When executive coaching fails

Over my career as an executive coach and organizational development practitioner I have had the opportunity to coach over 100 business leaders.  Through these coaching engagements I have learned a lot about what it takes to be a successful leader.  My number one conclusion is that the best leaders are life long learners.  They have a thirst for learning and are always striving to be better.

Coaching Conversation

Over the past few years I have had three bad coaching experiences.  Let me clarify, the experiences were not bad for me, it was the coachee in each case that did not benefit from the coaching.  In each of these engagements their organization’s and executive sponsors felt that the individuals would benefit from having a coach.  All three were senior level executives with good track records of performance.  In each case their leadership felt that they would benefit from understanding how their approaches impact those around them.  My goal from the start was to build rapport and to help them be more successful.

Whenever I start a new coaching engagement, I begin by personalizing the experience.  I explain my own career journey and how having a coach helped me and how I can serve as a confidant and third party perspective to help improve performance.  I use the analogy of coaching being like personal training.  I refer to this work as Mental Fitness. Even the best person trainer in the world cannot get you in better shape if you don’t want to do the work.  Coaching is quite similar.  I am a pretty successful coach, with a track record of significantly improving individual performance, but in each success story there was a coachee who was committed to the process.

As I build rapport with the coachee and work with them to define success for the coaching engagement I outline some ground rules which include:

  • Be on time for all sessions

  • Never cancel within 24 hours of the session

  • Be fully present (no phones or other distractions)

  • Confidentiality

  • Bring a willingness to be honest. 

I explain that while their organization has hired me, the coachee is my client and my goal is to make them successful.  Success might translate into happiness and that might not be possible at the current employer.  Regardless I need trust and I need them to be open with me.  I want this person to see me as a confidant.

In all three failed coaching engagements there was the same warning sign that things were not going to work.  Scheduling time for the coaching sessions is not my responsibility as the coach, it is the responsibility of the coachee.  In each of these cases, I had to spend time chasing the coachees trying to get on their calendars.  In all of my other coaching engagements, the coachees are willing and enthusiastic participants who see the benefit of having a coach and as a result they sought me out.  The three that did not succeed, never proactively sought me out.  One of them ultimately left his organization.  I could have been a resource and a thought partner as they worked through the dilemma of deciding to leave and seeking out another job.  As a coach who told that person, my goal is to be your trusted advisor, it is now clear we had no trust.

Setting up a successful coaching engagement requires three things:

1)      An organization that values coaching for performance.  I have coached in organizations where coaching has a negative stigma.  It is seen as the final step before exiting an employee.  I refuse to take on that type of work.  It does not fit with my coaching philosophy.  There  are other coaches out there that can do this work. 

2)      Coaching chemistry is essential.  The coachee must feel comfortable and connected with the coach.  I spend my first session with each coaching client focused on building rapport, getting to know each other and finding out common interests.  The chemistry leads to trust.  Once trust is established the relationship can go deeper and we can make progress on the blindspots and areas for improvement.  I also like to focus on the positives and to help my clients to shine a brighter light on the things they already do well.  I often question what they do best and what they do most.  If they are not spending enough time playing to their strengths, then we need to reallocate the way they are spending their time.

3)      An investment in continuous learning is the key to coaching success.  The coachee must want to be coached and to look forward to the coaching sessions.  Coaching is a gift and a significant investment that their organization is making in them.  It would be foolish not to take full advantage of the opportunity.


Through my experiences I can tell pretty quickly whether a coaching engagement will be successful or not.  In the case of the three coaching failures there was evidence from the start that it was not going to work.  I had frank conversations with each of the coachees and their executive sponsors explaining that I can only help if there is a dedication to the process and the work.  Commitment is the key to coaching success.